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Pros

Pro

Easy to use

A high level of attention to detail, intuitive suggestions and automation of common tasks make this application very easy to use.

Pro

Beautiful UI

Choice of color palette, icon glyph variety and animations create a design that is pleasurable to look at and does not get in the way.

Pro

Easy to to find old posts

With a good search and calendar view.

Pro

All the features you need

You can create more than one entry in one day. You have many styles and font choices. You can add photos, tags to your entries. Optionally, you can have pass-codes, reminders. You can opt to automatically add location and weather data. Search function built-in. Ability to export a portion or all entries to PDF.

Pro

Effortless syncing via iCloud

Between iOS and Mac.

Pro

2012 Mac App of the Year

Pro

Markdown support

Cons

Con

Subscription based

For former users, it's $24.99 per year.For new users, current discount is $34.99 per year while full price is $49.99 per year.

Con

Lack of DropBox and iCloud syncing

Con

No encryption

Data is stored in a plain-text XML file.

Con

Lacks Windows or Web support

Day One has no Windows or Web support, which can be inconvenient. For example, if users don't want to write a long journal entry on their phones and only have a Windows PC available as an alternative, they are not able to use it as a more practical alternative to write said post, not even using a web browser.

Con

Limited to one photo per entry

Currently, in both the mobile and Mac apps, only a single photo can be added to a journal entry.

Con

You need to purchase two separate subscriptions to sync your iPhone and Mac

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